“Sentimental” is one of the worst charges a critic can level at a book. Sometimes the insult is couched in “overly sentimental” or other adjectives and adverbs intended to soften the blow, but any novel that deals extensively with overt sadness or tenderness will likely have to weather such a criticism—or work hard to preemptively avoid it. The challenge is for those novels to rebut the label of sentimentality by proving that they are in fact not exaggerating the magnitude of suffering or slipping off into the embarrassing territory of self-indulgent storytelling, but rather to risk seeming sentimental in order to emotionally connect with readers. I would argue that Infinite Jest succeeds in hoeing very close to the boundaries of sentimentality without stepping over them. Though Wallace stated in interviews that Infinite Jest was about “sadness” of some form or the other, that sadness is not existential, but is a symptom of some other, deeper problem.

The Big Book of AA doesn’t give a shit about sentimentality. It starts out with the surprisingly unsentimental and straightforward tale of the group’s founder, Bill W. His story is written in the first person and the story’s goals are not primarily literary, though it is laced through with supremely sophisticated rhetoric. Bill W. writes simple, declarative lines like: “I was very lonely and again turned to alcohol,” which intentionally don’t tug at heartstrings or exaggerate or euphemize what is the foundation of all AA rock-bottom stories. If you’ve read Infinite Jest and heard enough of these AA rock-bottom stories, then Bill W.’s story is what you might expect: here was a successful Wall Street banker and alcohol ruined his life. He compresses much of the story down and even skips over the worst of his binges with candid phrases like “drinking caught up with me again” or “I went on a prodigious bender.”

Bill W.’s story is so sad because of the prolonged period wherein he knows he must, absolutely must stop drinking and yet is unable to find the resolve to quit drinking on his own. This genuinely perplexes him. He desperately wants to quit drinking, but every hospital he tries only keeps him dry for a few weeks. When he gets home, every time, he says “the courage to do battle was not there.” Simple self-knowledge or awareness is not what saves him from an early grave. It is a chance meeting with an old friend—a former alcoholic who has found religion.

Bill W.’s story lacks the syrupy sentimentality we might expect because ultimately, like Infinite Jest, it is a story about personal enlightenment. Hal’s own path towards enlightenment involves wrestling his way out of the cage of loneliness: “We enter a spiritual puberty where we snap to the fact that the great transcendent horror is loneliness, excluded encagement in the self. Once we’ve hit this age, we will now give or take anything, wear any mask, to fit, be part-of, not be Alone, we young.” It is this very encagement that shoots down the very thought of sentimentality or engaging deeply with one’s own emotions in order to make peace with them. “We are shown how to fashion masks of ennui and jaded irony at a young age where the face is fictile enough to assume the shape of whatever it wears. And then it’s stuck there, the weary cynicism that saves us from gooey sentiment and unsophisticated naïveté. Sentiment equals naïveté on this continent (at least since the Reconfiguration).”

Part of what Wallace is arguing here is that there is no such thing as authentically transcending sentimentality. To do so only denies one’s self access to true humanity. “Hal, who’s empty but not dumb, theorizes privately that what passes for hip cynical transcendence of sentiment is really some kind of fear of being really human, since to be really human, at least as he conceptualizes it is probably to be unavoidably sentimental and naive and goo-prone and generally pathetic, is to be in some basic interior way forever infantile, some sort of not-quite-right-looking infant dragging itself anaclitically around the map, with big wet eyes and froggy-soft skin, huge skull, gooey drool. One of the really American things about Hal, probably, is the way he despises what it is he’s really lonely for: this hideous internal self, incontinent of sentiment and need, that pulses and writhes just under the hip empty mask, anhedonia.” Another name for that hip, cool mask is irony. (“The worst thing about irony for me is that it attenuates emotion.”)

When Bill W. meets his formerly alcoholic friend and asks him how he has obtained this new-found sobriety, the friend says point blank “I’ve got religion.” This is one solution that Bill W. had not seriously considered. Something innate in him resisted the idea of giving up control of his life to a higher power. But yet he is interested in any program that would lead to lasting sobriety. This paradox is the climax of Bill’s story, which feels somewhat postmodern (especially for a story published in 1939) because the complex solution to saving his life turns out to be relatively simple. The whole point of AA is the attempt to find this power greater than (and thus outside of) one’s self. Bill looks at his now-sober friend and admits “It began to look as though religious people were right after all. Here was something at work in a human heart which had done the impossible. My ideas about miracles were drastically revised right then.” What allows Bill W. to change his mind about “God” and religion and higher powers is the tacit permission to choose his own conception of God. When the grace is unshackled from dogma, it transforms him for good.

The challenge of AA is to get new members to accept this basic fact: they must give up control of their lives to a Higher Power. The challenge of writing fiction about human emotions is to get readers to identify and empathize with characters instead of just pitying them.

In a 2013 interview, George Saunders talked about some conversations he’d had with David Foster Wallace and other writers about this very subject.

[Saunders] described making trips to New York in the early days and having “three or four really intense afternoons and evenings” with, on separate occasions, Wallace and Franzen and Ben Marcus, talking to each of them about what “the ultimate aspiration for fiction was.” Saunders added: “The thing on the table was emotional fiction. How do we make it? How do we get there? Is there something yet to be discovered? These were about the possibly contrasting desire to: (1) write stories that had some sort of moral heft and/or were not just technical exercises or cerebral games; while (2) not being cheesy or sentimental or reactionary.” {emphasis added}

To empathize, one must truly see outside of one’s self. It is a process of forgetting the self. The “destruction of self-centeredness” is the price to be paid for sobriety, AA will tell you. Part of that involves a traditionally religious idea of servitude, sacrificing for others over and over, “in myriad petty little unsexy ways, every day.” The alternative is not just the default setting we are stuck with (or literal godlessness–the ultimate solitude), it is the modern and postmodern rat race, “the constant gnawing sense of having had and lost some infinite thing.”

There is a myopic idea in the academic world of Wallace Studies that DFW & empathy has been “done.” Time to move along, now. Because they seem to lack sophistication and were covered early on, the recurring ideas of irony, sentimentality, and loneliness (or whatever) no longer hold appeal for the scholars who are, by the very nature of current scholarship, required to find some worthy topic that has been thus-far neglected. No one has written a dissertation on bird imagery in Wallace’s work so it’s suddenly “neglected” (for example) or maybe we do need more on Wallace’s work as it relates to race and gender and sexuality or analytic philosophy and political theory or any number of topics. But “empathy” was not just another topic Wallace was throwing out there for scholars to explore. This nexus of empathy-sentimentality-and “moral heft” gets to the DNA of who Wallace was as a writer and what he was hoping to accomplish in his art. Academics and critics can easily stand back and observe what it must take for a fictional character (which is basically what Wallace Himself is now anyway) to destroy “self-centeredness” but it is a uniquely human experience (rather than a purely cerebral one) for the realer, more enduring and sentimental part of one’s actual self to take charge and command that other part of the self to keep silent, “as if looking it levelly in the eye and saying, almost aloud, ‘Not another word.'”

But “empathy” was not just another topic Wallace was throwing out there for scholars to explore. This nexus of empathy-sentimentality-and “moral heft” gets to the DNA of who Wallace was as a writer and what he was hoping to accomplish in his art. Academics and critics can easily stand back and observe what it must take for a fictional character (which is basically what Wallace Himself is now anyway) to destroy “self-centeredness” but it is a uniquely human experience (rather than a purely cerebral one) for the realer, more enduring and sentimental part of one’s actual self to take charge and command that other part of the self to keep silent, “as if looking it levelly in the eye and saying, almost aloud, ‘Not another word.’”